JPH0332545B2 - - Google Patents

Info

Publication number: JPH0332545B2
Authority: JP; Japan
Prior art keywords: general formula; formula; carbon atoms; linear; derivative
Prior art date: 1981-12-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP57212073A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58113172A (ja

Inventor

Kabatsutsua Kuraujio

Orunera Chinchi Maria

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sigma Tau Industrie Farmaceutiche Riunite SpA

Original Assignee

Sigma Tau Industrie Farmaceutiche Riunite SpA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-12-03

Filing date

1982-12-01

Publication date

1991-05-13

1982-12-01 Application filed by Sigma Tau Industrie Farmaceutiche Riunite SpA filed Critical Sigma Tau Industrie Farmaceutiche Riunite SpA

1983-07-05 Publication of JPS58113172A publication Critical patent/JPS58113172A/ja

1991-05-13 Publication of JPH0332545B2 publication Critical patent/JPH0332545B2/ja

Status Granted legal-status Critical Current

Links

-1 halogen ion Chemical class 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 6
230000000510 mucolytic effect Effects 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
239000003434 antitussive agent Substances 0.000 claims description 2
229940124584 antitussives Drugs 0.000 claims description 2
239000003172 expectorant agent Substances 0.000 claims description 2
229940066491 mucolytics Drugs 0.000 claims description 2
JGBXDYVDPIRVLO-UHFFFAOYSA-N C(C)(=S)C(CC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O)C Chemical class C(C)(=S)C(CC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O)C JGBXDYVDPIRVLO-UHFFFAOYSA-N 0.000 claims 1
VWIOUOBDBMDNDG-UHFFFAOYSA-N C(C)(=S)CCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O Chemical class C(C)(=S)CCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O VWIOUOBDBMDNDG-UHFFFAOYSA-N 0.000 claims 1
WYRDFNRRMQYWOD-UHFFFAOYSA-N C(C)(=S)CCCCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O Chemical class C(C)(=S)CCCCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O WYRDFNRRMQYWOD-UHFFFAOYSA-N 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
239000002244 precipitate Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
230000001886 ciliary effect Effects 0.000 description 7
238000000034 method Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
239000000829 suppository Substances 0.000 description 6
239000000243 solution Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
206010036790 Productive cough Diseases 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
229940001584 sodium metabisulfite Drugs 0.000 description 4
235000010262 sodium metabisulphite Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
208000024794 sputum Diseases 0.000 description 4
210000003802 sputum Anatomy 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 3
230000028327 secretion Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 2
229960002295 acetylcarnitine hydrochloride Drugs 0.000 description 2
229960004308 acetylcysteine Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000010908 decantation Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
210000000981 epithelium Anatomy 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
210000005062 tracheal ring Anatomy 0.000 description 2
RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 description 1
XSJVWZAETSBXKU-UHFFFAOYSA-N 2-ethoxypropane Chemical compound CCOC(C)C XSJVWZAETSBXKU-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
HMSQBVHZHCCRCG-UHFFFAOYSA-N 6-bromo-3-hydroxy-4-oxo-3-[(trimethylazaniumyl)methyl]hexanoate Chemical compound BrCCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O HMSQBVHZHCCRCG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
XUJNEKJLAYXESH-UWTATZPHSA-N D-Cysteine Chemical compound SC[C@@H](N)C(O)=O XUJNEKJLAYXESH-UWTATZPHSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
206010062717 Increased upper airway secretion Diseases 0.000 description 1
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
208000018569 Respiratory Tract disease Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000000954 anitussive effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229960004203 carnitine Drugs 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
210000004081 cilia Anatomy 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000003419 expectorant effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
JDKQTIKEGOOXTJ-UHFFFAOYSA-N pent-4-enoyl chloride Chemical compound ClC(=O)CCC=C JDKQTIKEGOOXTJ-UHFFFAOYSA-N 0.000 description 1
208000026435 phlegm Diseases 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0031—Rectum, anus
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/009—Sachets, pouches characterised by the material or function of the envelope
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Dispersion Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Otolaryngology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Dermatology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP57212073A 1981-12-03 1982-12-01 チオアルカノイル−カルニチン誘導体、その製造法およびそれを有効成分とする医薬 Granted JPS58113172A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT49835A/81		1981-12-03
IT49835/81A IT1172127B (it)	1981-12-03	1981-12-03	Tioacil - carnitine procedimento per la loro preparazione e composizioni farmaceutiche che le contengono ad azione mucclitica

Publications (2)

Publication Number	Publication Date
JPS58113172A JPS58113172A (ja)	1983-07-05
JPH0332545B2 true JPH0332545B2 (de)	1991-05-13

Family

ID=11271675

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57212073A Granted JPS58113172A (ja)	1981-12-03	1982-12-01	チオアルカノイル−カルニチン誘導体、その製造法およびそれを有効成分とする医薬

Country Status (17)

Country	Link
US (1)	US4518613A (de)
JP (1)	JPS58113172A (de)
KR (1)	KR890000617B1 (de)
AT (1)	AT386408B (de)
BE (1)	BE894959A (de)
CA (1)	CA1188317A (de)
CH (1)	CH651019A5 (de)
DE (1)	DE3240112A1 (de)
DK (1)	DK535482A (de)
ES (1)	ES517888A0 (de)
FR (1)	FR2517672B1 (de)
GB (1)	GB2110670B (de)
IE (1)	IE53965B1 (de)
IT (1)	IT1172127B (de)
LU (1)	LU84496A1 (de)
NL (1)	NL8204638A (de)
SE (1)	SE453191B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3726945A1 (de) *	1987-08-13	1989-02-23	Dietl Hans	L-carnitinderivate der valproinsaeure und diese enthaltende arzneimittel
KR101552800B1 (ko) *	2014-10-24	2015-09-11	허태준	유류탱크의 결로 및 유류유출 방지장치
US11103588B2 (en) *	2017-06-06	2021-08-31	Wayne State University	Methods and compositions relating to carnitine-derived materials
KR102499363B1 (ko) *	2022-01-27	2023-02-13	주식회사 성문	컨테이너 외부 단열 방법

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5471024A (en) *	1977-11-17	1979-06-07	Nippon Yakin Kogyo Co Ltd	Adding method of cooling material
JPS5579821A (en) *	1978-12-11	1980-06-16	Japan Steel Works Ltd:The	Manufacture of low-carbon high-chromium alloy steel by heat-insulated furnace for molten steel
JPS56130419A (en) *	1980-03-15	1981-10-13	Nippon Steel Corp	Production of chromium-containing steel

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1116037B (it) *	1979-04-23	1986-02-10	Sigma Tau Ind Farmaceuti	Esteri e ammidi di acil carnitine loro procedimenti di preparazione e loro uso terapeutico
US4327111A (en) *	1980-07-14	1982-04-27	E. R. Squibb & Sons, Inc.	N-Substituted mercaptoacyl pripionamides

1981
- 1981-12-03 IT IT49835/81A patent/IT1172127B/it active
1982
- 1982-10-08 CH CH5917/82A patent/CH651019A5/it not_active IP Right Cessation
- 1982-10-22 US US06/436,190 patent/US4518613A/en not_active Expired - Fee Related
- 1982-10-22 IE IE2553/82A patent/IE53965B1/en not_active IP Right Cessation
- 1982-10-28 SE SE8206129A patent/SE453191B/sv not_active IP Right Cessation
- 1982-10-29 DE DE19823240112 patent/DE3240112A1/de active Granted
- 1982-11-03 GB GB08231450A patent/GB2110670B/en not_active Expired
- 1982-11-09 BE BE0/209435A patent/BE894959A/fr not_active IP Right Cessation
- 1982-11-09 CA CA000415170A patent/CA1188317A/en not_active Expired
- 1982-11-19 KR KR8205236A patent/KR890000617B1/ko active
- 1982-11-24 FR FR8219673A patent/FR2517672B1/fr not_active Expired
- 1982-11-30 NL NL8204638A patent/NL8204638A/nl not_active Application Discontinuation
- 1982-12-01 LU LU84496A patent/LU84496A1/xx unknown
- 1982-12-01 JP JP57212073A patent/JPS58113172A/ja active Granted
- 1982-12-02 AT AT0438182A patent/AT386408B/de not_active IP Right Cessation
- 1982-12-02 ES ES517888A patent/ES517888A0/es active Granted
- 1982-12-02 DK DK535482A patent/DK535482A/da not_active Application Discontinuation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5471024A (en) *	1977-11-17	1979-06-07	Nippon Yakin Kogyo Co Ltd	Adding method of cooling material
JPS5579821A (en) *	1978-12-11	1980-06-16	Japan Steel Works Ltd:The	Manufacture of low-carbon high-chromium alloy steel by heat-insulated furnace for molten steel
JPS56130419A (en) *	1980-03-15	1981-10-13	Nippon Steel Corp	Production of chromium-containing steel

Also Published As

Publication number	Publication date
US4518613A (en)	1985-05-21
GB2110670A (en)	1983-06-22
KR890000617B1 (ko)	1989-03-22
SE453191B (sv)	1988-01-18
DE3240112A1 (de)	1983-06-09
JPS58113172A (ja)	1983-07-05
SE8206129L (sv)	1983-06-04
LU84496A1 (fr)	1983-06-13
SE8206129D0 (sv)	1982-10-28
IT1172127B (it)	1987-06-18
IE822553L (en)	1983-06-03
CA1188317A (en)	1985-06-04
CH651019A5 (it)	1985-08-30
FR2517672A1 (fr)	1983-06-10
GB2110670B (en)	1985-06-12
DE3240112C2 (de)	1992-06-25
IE53965B1 (en)	1989-04-26
ATA438182A (de)	1988-01-15
ES8401752A1 (es)	1984-01-01
KR840002351A (ko)	1984-06-25
FR2517672B1 (fr)	1987-06-19
NL8204638A (nl)	1983-07-01
ES517888A0 (es)	1984-01-01
DK535482A (da)	1983-06-04
IT8149835A0 (it)	1981-12-03
AT386408B (de)	1988-08-25
BE894959A (fr)	1983-03-01

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FI92388C (fi)	1994-11-10	Menetelmä karbasykliinianalogien terapeuttisesti käyttökelpoisten syklodekstriiniklatraattien valmistamiseksi
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EP4161524A1 (de)	2023-04-12	Verfahren zur behandlung einer coronavirus-infektion
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Morris et al.	1950	The distribution of radioactivity following the feeding of carbon 14-labeled 2-acetylaminofluorene to rats
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CN1481246A (zh)	2004-03-10	炎症性呼吸道疾病的预防/治疗剂
TW202246206A (zh)	2022-12-01	一種曲前列環素衍生物及其用途
JPH0332545B2 (de)	1991-05-13
CA2145229A1 (en)	1995-09-30	Suppressory compositions against hepatic metastases of tumors
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KR860001902B1 (ko)	1986-10-24	메르캅토 아실 카르니틴 에스테르류의 제조방법
CA2563684A1 (en)	2005-11-03	Preventive and/or therapeutic agent for chronic sinusitis
KR860001311B1 (ko)	1986-09-13	2-테노일메르캅토프로피온일글리신과 치환 히드록시벤젠류와의 에스테르 제조방법
JP7393052B2 (ja)	2023-12-06	去痰化合物、その製造方法及び使用
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CN112999215B (zh)	2024-06-21	呋喃酮糖苷类化合物的应用
FI62283B (fi)	1982-08-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-2'-karboxifenyl-4-klorantranilsyraderivat
US4078090A (en)	1978-03-07	(Carboxymethylthio)acetic acid and salts thereof used as mucolytic agents
RU2726119C1 (ru)	2020-07-09	Новые производные полиолов, их применение, фармацевтическая композиция на их основе
Chou	1931	The alkaloids of gelsemium. I. Gelsemine and gelsemicine